Cobalt-Catalyzed Benzylic Borylation: Enabling Polyborylation and Functionalization of Remote, Unactivated C(sp3)–H Bonds | Zendy

W. Neil Palmer | Zendy; Jennifer V. Obligacion | Zendy; Iraklis Pappas | Zendy; Paul J. Chirik | Zendy

Open Access

Cobalt-Catalyzed Benzylic Borylation: Enabling Polyborylation and Functionalization of Remote, Unactivated C(sp³)–H Bonds

Author(s) -

W. Neil Palmer,

Jennifer V. Obligacion,

Iraklis Pappas,

Paul J. Chirik

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b12249

Subject(s) - chemistry , borylation , surface modification , cobalt , catalysis , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , polymer chemistry , aryl , alkyl

Cobalt dialkyl and bis(carboxylate) complexes bearing α-diimine ligands have been synthesized and demonstrated as active for the C(sp(3))-H borylation of a range of substituted alkyl arenes using B2Pin2 (Pin = pinacolate) as the boron source. At longer reaction times, rare examples of polyborylation were observed, and in the case of toluene, all three benzylic C-H positions were functionalized. Coupling benzylic C-H activation with alkyl isomerization enabled a base-metal-catalyzed method for the borylation of remote, unactivated C(sp(3))-H bonds.

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